US4493852A - 1,1-Bis (thioalkyl) alkyl-2,4-diene as a flavoring agent - Google Patents

1,1-Bis (thioalkyl) alkyl-2,4-diene as a flavoring agent Download PDF

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Publication number
US4493852A
US4493852A US06/602,095 US60209584A US4493852A US 4493852 A US4493852 A US 4493852A US 60209584 A US60209584 A US 60209584A US 4493852 A US4493852 A US 4493852A
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foodstuff
bis
group
diene
flavor
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US06/602,095
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Paul R. Zanno
Thomas H. Parliment
Robert J. Soukup
Richard P. McNaught
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General Foods Corp
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General Foods Corp
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Assigned to GENERAL FOODS CORPORATION A CORP OF DE reassignment GENERAL FOODS CORPORATION A CORP OF DE ASSIGNMENT OF ASSIGNORS INTEREST. Assignors: MC NAUGHT, RICHARD P., PARLIMENT, THOMAS H., SOUKUP, ROBERT J., ZANNO, PAUL R.
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    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
    • A23L27/20—Synthetic spices, flavouring agents or condiments
    • A23L27/24—Synthetic spices, flavouring agents or condiments prepared by fermentation
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
    • A23L27/20—Synthetic spices, flavouring agents or condiments
    • A23L27/202—Aliphatic compounds
    • A23L27/2022—Aliphatic compounds containing sulfur

Definitions

  • This invention relates to a composition which imparts or enhances the flavor of foodstuffs. More particularly a flavoring composition has been discovered which imparts or enhances the meaty, chicken-like, fatty and pork-like flavor, aroma and character of foodstuffs. A process is also disclosed for preparing the flavoring composition.
  • this invention involves adding as a flavoring composition an effective amount of a flavoring compound having the following structure: ##STR2## wherein R 1 is an alkyl group of 1 to 7 carbon atoms; and R 2 and R 3 are chosen from the group consisting of an alkyl group of 1 to 3 carbon atoms.
  • the bis(thioalkyl) compound is prepared by reacting aliphatic polyene aldehydes with alkyl thiols with the reaction rate being increased by use of appropriate organic solvents and catalysts.
  • This invention is directed to a flavoring composition which enhances or imparts unique flavor characteristics in foods.
  • the flavoring composition comprises use of an effective amount of the compound 1,1-bis(thioalkyl)alkyl-2,4-diene and has the following structure: ##STR3## wherein R 1 is an alkyl group of 1 to 7 carbon atoms; and R 2 and R 3 are chosen from the group consisting of an alkyl group of 1 to 3 carbon atoms.
  • R 1 is a butyl or pentyl group and R 2 and R 3 are methyl group.
  • R 2 and R 3 can be different groups although preferably they are identical.
  • the flavoring composition of this invention includes, but is not limited to, the following flavoring compounds: 1,1-bis(thiomethyl)nona-2,4-diene; 1,1-bis(thiomethyl)deca-2,4-diene; 1,1-bis(thioethyl)nona-2,4-diene; 1,1-bis(thiopropyl)deca-2,4-diene; and 1-thiomethyl-1-thioethyl-octa-2,4-diene.
  • the flavoring composition of this invention imparts a fatty, meaty, chicken-like, pork-like quality, flavor, aroma and character, with some of the compounds imparting a green, vegetable-like character when added in effective amounts to a food product.
  • the type of flavor may vary slightly depending upon the amount of the flavoring composition employed, with higher amounts generally imparting a more pork, fatty flavor and the lower amounts imparting a meaty, chickeny flavor.
  • the flavoring composition can be effectively incorporated in any one of a number of foodstuffs such as sauces, gravies, seasonings, stuffing mixes, soups, meats (including meat analogs and pet foods), or beverages.
  • the level at which the flavoring compound is effective in foodstuffs in generally within the range of 0.1 to 100 parts per million, preferably 1 to 25 parts per million of the foodstuff.
  • aliphatic polyene aldehydes react with alkyl thiols when mixed together to form 1,1-bis(thioalkyl)alkyl-2,4-dienes.
  • the rate of reaction of these compounds can be increased by using an appropriate organic solvent (CHCl 3 , CH 2 Cl 2 , ethyl ether) and BF 3 , Lewis acids (AlCl 3 , etc.) or mineral acids (HCl, etc.) as a catalyst.
  • the flavoring composition containing the bis(thioalkyl) compound of this invention can be combined with other natural or synthetic flavors to provide a balanced flavor depending upon the desired end use.
  • the flavoring composition can also be fixed on or in a carrier to provide a dry flowable form by common methods, such as by spray or freeze drying the flavoring composition with a carrier such as dextrin, gum arabic, etc.
  • the flavoring composition 1,1-bis(thiomethyl)deca-2,4-diene was incorporated into the following foodstuffs and at the following levels with the resultant flavor and aroma:

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  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Health & Medical Sciences (AREA)
  • Nutrition Science (AREA)
  • Chemical & Material Sciences (AREA)
  • Food Science & Technology (AREA)
  • Polymers & Plastics (AREA)
  • Biotechnology (AREA)
  • Seasonings (AREA)

Abstract

A flavoring composition comprising an effective amount of a compound having the following structure: ##STR1## wherein R1 is an alkyl group of 1 to 7 carbon atoms; and R2 and R3 are chosen from the group consisting of hydrogen and an alkyl group of 1 to 3 carbon atoms. These compounds have been found to impart a fatty, meaty, chicken-like and pork-like quality, flavor and aroma when added in effect amounts to food products.

Description

This application is a continuation of application Ser. No. 304,394, filed 9/21/81, now abandoned.
BACKGROUND OF THE INVENTION
This invention relates to a composition which imparts or enhances the flavor of foodstuffs. More particularly a flavoring composition has been discovered which imparts or enhances the meaty, chicken-like, fatty and pork-like flavor, aroma and character of foodstuffs. A process is also disclosed for preparing the flavoring composition.
Food products enhanced with poultry-like or pork-like flavors are known in the art and have long been used. There is considerable demand for these flavors in which the actual pork or poultry meat is not needed or is actually undesirable. For example, in the preparation of some sauces and purees a poultry or pork flavor is desired, but it is necessary to cook the food with the desired meat and then remove the meat by straining it, or some similar operation to obtain the final product ready for use. While this method for preparing a flavored sauce of puree is effective it is time consuming and expensive.
Additionally, where weight, space and/or storage capability are a problem, e.g. when a convenience food is prepared, the presence of the actual meat may be undesirable because it will deteriorate in storage and spoil the food. Moreover, there are occasions when sterilizing or otherwise preserving the natural product is extremely deleterious to the flavor of the natural material and the desired natural flavor is lost.
Thus, it is a feature of this invention to provide a flavoring composition which can be incorporated in a wide range of foodstuffs.
It is a further feature of this invention to provide a process for preparing the flavoring composition.
SUMMARY OF THE INVENTION
Briefly, this invention involves adding as a flavoring composition an effective amount of a flavoring compound having the following structure: ##STR2## wherein R1 is an alkyl group of 1 to 7 carbon atoms; and R2 and R3 are chosen from the group consisting of an alkyl group of 1 to 3 carbon atoms. The bis(thioalkyl) compound is prepared by reacting aliphatic polyene aldehydes with alkyl thiols with the reaction rate being increased by use of appropriate organic solvents and catalysts.
DETAILED DESCRIPTION OF THE INVENTION
This invention is directed to a flavoring composition which enhances or imparts unique flavor characteristics in foods. The flavoring composition comprises use of an effective amount of the compound 1,1-bis(thioalkyl)alkyl-2,4-diene and has the following structure: ##STR3## wherein R1 is an alkyl group of 1 to 7 carbon atoms; and R2 and R3 are chosen from the group consisting of an alkyl group of 1 to 3 carbon atoms. Preferably, R1 is a butyl or pentyl group and R2 and R3 are methyl group. R2 and R3 can be different groups although preferably they are identical. When the compounds have alkyl groups with higher chain lengths than 7 carbon atoms for R1, or higher than 3 carbon atoms for R2 and R3, the resultant compounds do not have the desired flavor, aroma and character. Within the above structure the flavoring composition of this invention includes, but is not limited to, the following flavoring compounds: 1,1-bis(thiomethyl)nona-2,4-diene; 1,1-bis(thiomethyl)deca-2,4-diene; 1,1-bis(thioethyl)nona-2,4-diene; 1,1-bis(thiopropyl)deca-2,4-diene; and 1-thiomethyl-1-thioethyl-octa-2,4-diene.
The flavoring composition of this invention imparts a fatty, meaty, chicken-like, pork-like quality, flavor, aroma and character, with some of the compounds imparting a green, vegetable-like character when added in effective amounts to a food product. The type of flavor may vary slightly depending upon the amount of the flavoring composition employed, with higher amounts generally imparting a more pork, fatty flavor and the lower amounts imparting a meaty, chickeny flavor. The flavoring composition can be effectively incorporated in any one of a number of foodstuffs such as sauces, gravies, seasonings, stuffing mixes, soups, meats (including meat analogs and pet foods), or beverages. The level at which the flavoring compound is effective in foodstuffs in generally within the range of 0.1 to 100 parts per million, preferably 1 to 25 parts per million of the foodstuff.
To prepare the flavoring composition aliphatic polyene aldehydes react with alkyl thiols when mixed together to form 1,1-bis(thioalkyl)alkyl-2,4-dienes. The rate of reaction of these compounds can be increased by using an appropriate organic solvent (CHCl3, CH2 Cl2, ethyl ether) and BF3, Lewis acids (AlCl3, etc.) or mineral acids (HCl, etc.) as a catalyst.
The flavoring composition containing the bis(thioalkyl) compound of this invention can be combined with other natural or synthetic flavors to provide a balanced flavor depending upon the desired end use. The flavoring composition can also be fixed on or in a carrier to provide a dry flowable form by common methods, such as by spray or freeze drying the flavoring composition with a carrier such as dextrin, gum arabic, etc.
EXAMPLE 1
To a cooled (0° C.) solution of 25 ml. nona-2,4-dienal in 100 ml. of CHCl3 was added 25 ml of methyl mercaptan. To this solution (at 0° C.) was then added 0.5 ml. of BF3 : etherate. The mixture was allowed to come to room temperature, then stirred for 1 hour. After this time the mixture was distilled under vacuum giving 15 gm of 1,1 bis(thiomethyl)nona-2,4 diene.
EXAMPLE 2
To a cooled (0° C.) solution of 25 ml. of deca-2,4-dienal in 100 ml. of CHCl3 was added 25 ml. of methyl mercaptan. To this solution (at 0° F.) was then added 0.5 ml of BF3 : etherate. The mixture was allowed to come to RT then stirred for 1 hour. After this time the mixture was distilled under vacuum giving 12.5 gm of 1,1 bis(thiomethyl)deca-2,4-diene.
EXAMPLE 3
The flavoring composition 1,1-bis(thiomethyl)deca-2,4-diene was incorporated into the following foodstuffs and at the following levels with the resultant flavor and aroma:
______________________________________                                    
            Level of                                                      
            Flavoring     Observed                                        
Foodstuff   Composition   Flavor                                          
______________________________________                                    
Oriental    6.6 ppm       meaty, pork-like                                
Noodles                   soup flavor                                     
(hydrated dry                                                             
            9.9 ppm       more pork-like                                  
mix)                      flavor, chicken-                                
                          like, slightly                                  
                          fatty                                           
Beef Rice Mix                                                             
            20 ppm        more savory,                                    
(hydrated dry             fatty, meaty                                    
mix)                      flavor                                          
Meatless Chow                                                             
            10 ppm        more savory                                     
Mein (canned)             meaty flavor                                    
______________________________________
EXAMPLE 4
The compound 1,1-bis(thiomethyl)alkyl-2,4-diene with the following structure: ##STR4## was evaluated for organoleptic properties varying the R1 substituent with the following results:
______________________________________                                    
R.sub.1          Organoleptic Evaluation                                  
______________________________________                                    
CH.sub.3         Green/Fatty/Oily/Fried                                   
CH.sub.3 CH.sub.2                                                         
                 Green/Vegetable-like                                     
CH.sub.3 (CH.sub.2).sub.3                                                 
                 Chicken-like/Pork-like/                                  
                 Brothy/Fatty                                             
CH.sub.3 (CH.sub.2).sub.4                                                 
                 Chicken-like/Pork-like/                                  
                 Brothy/Fatty                                             
CH.sub.3 (CH.sub.2).sub.5                                                 
                 Weak Fatty/Oily                                          
______________________________________

Claims (6)

What is claimed is:
1. A foodstuff selected from a group consisting of soup, meat and stuffing mix comprising an amount of a flavoring compound within the range of 0.1 to 100 part ppm of the foodstuff, said flavoring compound having the following structure: ##STR5## wherein R1 is an alkyl group of 1 to 7 carbon atoms; and R2 and R3 are an alkyl group of 1 to 3 carbon atoms.
2. Foodstuff of claim 1 wherein R1 is chosen from the group consisting of a butyl group and a pentyl group.
3. Foodstuff of claim 1 wherein the amount of the flavoring composition is within the range of 1 to 25 ppm of the foodstuff.
4. Foodstuff of claim 1 further comprising other natural or synthetic flavors.
5. Foodstuff of claim 1 wherein the flavor compound is fixed on a carrier wherein said carrier is selected from a group consisting of dextrose and gum.
6. Foodstuff of claim 1 wherein the flavoring compound is chosen from the group consisting of 1,1-bis(thiomethyl)nona-2,4-diene and 1,1-bis(thiomethyl)deca-2,4-diene.
US06/602,095 1981-09-21 1984-04-20 1,1-Bis (thioalkyl) alkyl-2,4-diene as a flavoring agent Expired - Lifetime US4493852A (en)

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Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4565707A (en) * 1985-05-08 1986-01-21 International Flavors & Fragrances Inc. Flavoring with dialkylthioalkenes, dialkylthioalkylcycloalkenes and monoalkylthioalkenylcycloalkenes
US4571344A (en) * 1985-04-23 1986-02-18 International Flavors & Fragrances Inc. Flavoring with dithioethers of 2-phenyl-2-alkenals
US4658067A (en) * 1985-05-08 1987-04-14 International Flavors & Fragrances Inc. Dialkylthioalkenes, dialkylthioalkylcycloalkenes and monoalkylthioalkenylcycloalkenes and organoleptic uses thereof
US20050112259A1 (en) * 2003-11-26 2005-05-26 Fernando Qvyjt Pet food composition having enhanced palatability

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2594379A (en) * 1950-09-16 1952-04-29 Standard Brands Inc Flavoring materials and method of preparing the same
US3258493A (en) * 1962-09-11 1966-06-28 Nat Distillers Chem Corp alpha, alpha'-bis(laurylthio)-p-xylene
US3509182A (en) * 1966-03-24 1970-04-28 Pyrethrum Board Of Kenya The Production of acetals and mercaptals
US3852481A (en) * 1970-03-10 1974-12-03 Gen Foods Corp Synthetic grinder gas aromas and processes

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2594379A (en) * 1950-09-16 1952-04-29 Standard Brands Inc Flavoring materials and method of preparing the same
US3258493A (en) * 1962-09-11 1966-06-28 Nat Distillers Chem Corp alpha, alpha'-bis(laurylthio)-p-xylene
US3509182A (en) * 1966-03-24 1970-04-28 Pyrethrum Board Of Kenya The Production of acetals and mercaptals
US3852481A (en) * 1970-03-10 1974-12-03 Gen Foods Corp Synthetic grinder gas aromas and processes

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4571344A (en) * 1985-04-23 1986-02-18 International Flavors & Fragrances Inc. Flavoring with dithioethers of 2-phenyl-2-alkenals
US4565707A (en) * 1985-05-08 1986-01-21 International Flavors & Fragrances Inc. Flavoring with dialkylthioalkenes, dialkylthioalkylcycloalkenes and monoalkylthioalkenylcycloalkenes
US4658067A (en) * 1985-05-08 1987-04-14 International Flavors & Fragrances Inc. Dialkylthioalkenes, dialkylthioalkylcycloalkenes and monoalkylthioalkenylcycloalkenes and organoleptic uses thereof
US20050112259A1 (en) * 2003-11-26 2005-05-26 Fernando Qvyjt Pet food composition having enhanced palatability

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